How Younger Salespeople Can Win Over Older Customers

Executive Summary

More companies are putting younger team members–millennials–in charge of connecting with buyers at earlier stages of the sales cycle. This creates a challenge of “experience asymmetry.” It occurs when young salespeople find themselves pitching older decision makers who have much more experience than they do. Often, the potential buyers are wary, skeptical that the inexperienced representative can offer them ways to improve how they do their jobs or run their businesses. (With LinkedIn at our fingertips, most people can learn the experience levels and approximate ages of professionals in a matter of seconds.) This piece describes three presentation techniques salespeople can use to help overcome skepticism rooted in the clients’ perception of the rep’s lack of experience.

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As companies build out their sales organizations, I find that more and more are putting younger team members–millennials–in charge of connecting with buyers at earlier stages of the sales cycle. That helps explain why, as I train and advise sales teams, many report a rising inter-generational challenge.

I call it experience asymmetry. These young salespeople find themselves pitching older decision makers who have much more experience than they do. Often, the potential buyers are wary, skeptical that the inexperienced representative can offer them ways to improve how they do their jobs or run their businesses. (With LinkedIn at our fingertips, most people can learn the experience levels and approximate ages of professionals in a matter of seconds.)

I’m able to train people on how to handle these situations partly because of my own experience. Early in my career, I was a sales engineer for a high-growth software company. Our products were designed to help keep track of employees’ work hours and schedules. Our target customers included many of the world’s largest manufacturing organizations.

I was 25 years old. Many potential clients I was pitching had worked in the industry, and even at their company, for decades, and had used the same legacy IT systems for all of that time. At one point, I was kicking off a discovery session with a manufacturer of heavy-duty construction equipment. The boardroom was full of executives. One of them turned to me and said with a smile, “I bet we have systems in place here that are older than you!” Laughter spread throughout the room.

Fortunately, I was prepared. I laughed too, showing I could appreciate the joke. Then I launched into the conversation. By the end, the client was happy, and even turned that initial skepticism on its head, saying, “Wow, you know what? I think if we had an older guy come in to tell us about the latest technology, we wouldn’t have believed him!” Of course, that’s not good if it’s literally true, but I took it as a well-intended joke.

Most importantly: we made the sale.

There are three key steps I followed–then, and many times since–to overcome experience asymmetry. They are the steps I teach and recommend to this day:

Know their pain points. Nothing helps prospects realize “this person can actually help me” better than a seller who comes equipped with well-articulated points that speak to the problems they’re facing — their pain points. To do this, you should know your market well enough to be able to label the client’s fears and concerns. (Former FBI hostage negotiator Chris Voss discusses this in his book Never Split the Difference.)

As I stood in that boardroom, I explained the challenge these folks were facing. They had spent years struggling to calculate their employees’ pay correctly as union and state regulations changed. I described the friction their legacy IT created in this area, and how our software resolved it. The perception that my youth meant a lack of knowledge disappeared.

Invoke the credibility of others. It’s tempting in these situations to try to highlight your own experience by starting sentences with, “What I’ve found is” or “I think.” Don’t. The customer generally doesn’t care what you think, and those phrases only serve as reminders of your relative lack of experience.

Instead, continuously put the focus on what experts have to say. Start with phrases like “Our customers have consistently found that” or “What we’ve seen time and time again is.” When I was selling software, I had worked with other companies facing similar pain points, and was able to cite specific experiences and credible industry statistics to establish expertise.

Present arguments with conviction.How you pitch is every bit as important as what you say. Although customers may not consider you authoritative, they will still respond to enthusiasm. Presenting your case with conviction shows that you’re not just reciting a pitch you memorized, but sharing your own definitive knowledge.

Take the example of a waiter I once had. I asked him how the tenderloin was. Without hesitation, he replied, “It’s the absolute best thing on the menu in my opinion.” He then described the maple syrup reduction and parsnip mash side dish. Four of the six people in my party immediately changed their orders to the tenderloin.

As I stood in the boardroom that day, I was thoroughly convinced that our solution was not only the best on the market, but the best fit for my customer. Whatever they thought of my credibility, my conviction shined through.

When facing experience asymmetry, keep in mind that it’s largely about respect. Just as you want prospects to know they can trust you, prospects want to know that you appreciate their seniority and experience. As with all things in sales, it’s important to listen more than you speak, ask lots of questions, and let the customer know that you’re learning from them. The more you do that, the more they’ll trust you to deliver value.